Spiro[indene-1,4'-piperidine] → 1''N-(2-adamantyl)spiro[1H-indene-1,4''-(hexahydropyridine)]-1''-carboxamide

HRID 1534790Notes

Reaction equation

HRID 1534790 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=[CH:7]2)[CH2:3][CH2:2]1.[CH:15]12[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:23][CH:17]([CH2:18]3)[CH:16]1[N:25]=[C:26]=[O:27])[CH2:22]2>C(Cl)Cl.C(N(CC)CC)C>[CH:17]12[CH2:23][CH:21]3[CH2:20][CH:19]([CH2:24][CH:15]([CH2:22]3)[CH:16]1[NH:25][C:26]([N:1]1[CH2:6][CH2:5][C:4]3([C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[CH:8]=[CH:7]3)[CH2:3][CH2:2]1)=[O:27])[CH2:18]2

Participants

5

Reactant 2

HCID 10330052Spiro[indene-1,4'-piperidine]HCID 128826302-Isocyanatoadamantane2×

Product 1

HCID 199083151''N-(2-adamantyl)spiro[1H-indene-1,4''-(hexahydropyridine)]-1''-carboxamide

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

Spiro(1H-indene-1,4'-piperidine) (20 mg, 0.108 mmol) and 2-adamantyl isocyanate (18 mg, 0.10 mmol) were combined in CH2Cl2 and stirred overnight at ambient temperature. An additional 5 mg (0.028 mmol) of 2-adamantyl isocyanate and 2 drops of triethylamine were added and the mixture again stirred overnight at ambient temperature. The mixture was chromatographed directly on a silica gel column eluted with CH2Cl2 followed by 0.5% and 1% methanol in CH2Cl2. The product fractions were combined and evaporated to dryness in vacuo, and the residue was crystallized from petroleum ether to provide the title compound as a solid: (mp 189°-191°).

Workup

  1. customthe mixture again stirred overnight
  2. customat ambient temperature
  3. customThe mixture was chromatographed directly on a silica gel column
  4. washeluted with CH2Cl2
  5. customevaporated to dryness in vacuo
  6. customthe residue was crystallized from petroleum ether

Sources & evidence

ORD record
ord-8cec7cfe0949407b929ef22d27607d8a
Source dataset
uspto-grants-1992_02
Patent number
US05091387

Reaction notes

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